Winter Haven holiday lettings

We found 1,062 holiday rentals — enter your dates for availability
Discover a selection of 56 homes and other holiday rentals in Winter Haven that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you need and want for your stay, which might include cable TV and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Winter Haven

Showing deals for:6 Nov - 13 Nov

Image gallery for Beautiful luxury golf villa with private pool & spa

Pool
9.4 out of 10, Exceptional, (63 reviews)
Exceptional
(63 reviews)

Beautiful luxury golf villa with private pool & spa

Haines City

8% off
Price is £1,174
for 7 nights, 1 villa
£168 per night
includes taxes & fees
Beautiful luxury golf villa with private pool & spa

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Winter Haven

  • LEGOLAND Florida Resort: A thrilling amusement park perfect for families, featuring rides, attractions, and interactive experiences themed around LEGO.
  • Chain of Lakes: Enjoy scenic views and outdoor activities such as boating and fishing across this picturesque network of lakes.
  • Bok Tower Gardens: A serene botanical garden offering beautiful landscapes and a stunning singing tower, ideal for relaxation and exploration.
  • Community Spirit: Experience the warmth and friendliness of locals, making Winter Haven a welcoming destination for visitors.
  • Private Accommodation: A variety of comfortable vacation homes and villas provide convenient lodging options for families and groups.

Popular types of accommodation in Winter Haven

Winter Haven, Florida is a charming city known for its stunning lakes and vibrant community. Visitors can explore the famous LEGOLAND Florida Resort, enjoy leisurely strolls around the picturesque Chain of Lakes, or indulge in outdoor activities at Bok Tower Gardens. For your stay, consider a range of houses, villas, or condos that provide comfort and convenience, perfect for families and groups alike. Experience the warmth of Winter Haven and create lasting memories in this delightful destination.

  • Houses: Ideal for families or groups, these spacious residences offer a home-like atmosphere with all the comforts you need for a memorable stay.
  • Villas: Luxurious and often featuring private pools, villas provide a sophisticated retreat perfect for relaxation and leisure.
  • Condos: Conveniently located, condos offer a blend of comfort and amenities, perfect for both short and extended stays.
  • Apartments: Offering a cosy and practical option, apartments are great for those seeking a more residential experience.
  • Cottages: Charming and quaint, cottages provide a picturesque getaway, often surrounded by nature.**

Top attractions in and around Winter Haven

Winter Haven, Florida, is a delightful destination for families and outdoor enthusiasts, boasting stunning lakes, urban parks, and exciting amusement parks. Visitors can enjoy a variety of experiences that cater to both adventure seekers and those looking for a relaxing beach atmosphere. With its scenic landscapes and family-friendly attractions, Winter Haven offers a perfect blend of outdoor fun and leisure for tourists seeking memorable holiday experiences.

  • LEGOLAND® Florida: This vibrant amusement park offers a world of adventure and creativity, perfect for families. With interactive rides, shows, and LEGO-themed attractions, it promises a fun-filled day for visitors of all ages.
  • The Circle B Bar Reserve: An outdoor haven for nature lovers, this reserve features scenic trails and diverse wildlife. Explore the natural beauty and enjoy a peaceful escape into Florida's unique ecosystems.
  • Lake Conine: A picturesque lake ideal for relaxation, Lake Conine boasts stunning views and a tranquil atmosphere, making it a perfect spot for a romantic picnic or a leisurely day by the water.

Things to do recommended for couples

Winter Haven offers charming experiences for couples, such as a leisurely boat ride on the scenic Chain of Lakes, or a romantic stroll through the beautiful Bok Tower Gardens, where you can admire stunning views and enchanting landscapes. Enjoy intimate dining at local eateries for a perfect evening.

Things to do recommended for families

Families visiting Winter Haven can have a delightful day at LEGOLAND Florida Resort, where kids can enjoy thrilling rides and creative LEGO attractions. The nearby Safari Wilderness offers an exciting opportunity to see exotic animals up close on a unique safari tour, perfect for all ages.

Things to do recommended for groups

Groups visiting Winter Haven can enjoy a thrilling day at LEGOLAND Florida Resort, explore the picturesque Chain of Lakes with a scenic boat tour, and unwind at local parks like Bok Tower Gardens for a taste of natural beauty and tranquillity.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Winter Haven

If you’re travelling with a group, family, or pets, or if you’re seeking longer stays, be sure to refine your search according to your key preferences. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Winter Haven with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Winter Haven with young kids: Travelling with young children can present its own set of challenges. It’s important to prioritise their comfort and safety, along with suitable facilities, such as a private swimming pool. Additionally, it’s wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Winter Haven: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortably at home.
  • Planning for a long term stay visiting Winter Haven: If you're in search of holiday rentals with offers for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Winter Haven

Winter Haven, Florida, offers a delightful blend of family-friendly attractions and outdoor adventures. Visitors can explore the stunning Chain of Lakes, perfect for boating and fishing, or enjoy the thrills at LEGOLAND Florida Resort. With its welcoming atmosphere and friendly locals, Winter Haven is an ideal destination for family getaways, providing a relaxing escape in Central Florida. Embrace the vibrant community while enjoying the beautiful landscapes and numerous recreational activities available in this charming city.

  • Eloise: Nestled within the Winter Haven area, Eloise is a charming village known for its family-friendly atmosphere and outdoor adventures. This picturesque locale is perfect for those seeking an escape into nature, with numerous recreational areas and resorts nearby. Visitors can enjoy a variety of attractions, including a renowned theme park and beautiful bays, making it an ideal spot for family outings and outdoor activities. The quaint neighbourhood vibe adds to its appeal, offering a delightful experience for tourists looking to explore the beauty of central Florida.
  • Davenport: Located approximately 21km from Winter Haven, Davenport is a vibrant city that caters to families and those seeking entertainment-themed experiences. The area boasts an array of resorts and golf courses, making it a haven for leisure seekers. Davenport is home to notable landmarks such as theme parks and film studios, providing ample entertainment options for visitors. Whether you're teeing off on the golf course or enjoying a day at the beach, Davenport promises a variety of activities that will make your stay memorable.
  • Cypress Gardens: Situated close to Winter Haven, Cypress Gardens is another delightful village that attracts families and outdoor enthusiasts. Known for its adventure-oriented experiences, this area features a mix of resorts, amusement parks, and golf facilities. Visitors can explore local attractions, including a popular theme park and nearby beaches, perfect for a day of fun in the sun. The presence of sports facilities adds to the excitement, making Cypress Gardens a well-rounded destination for those seeking adventure and leisure in a picturesque setting.

Best time to go to Winter Haven

If you're planning a trip to Winter Haven, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in March to April and September, while off-peak times, like August and October to November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January60.4°F (15.8°C)Light RainMostly SunnyAverageSlightly Low
February64.4°F (18.0°C)No Rain (Dry)Mostly SunnyAverageSlightly Low
March67.5°F (19.7°C)Light RainMostly SunnySlightly HighAverage
April72.9°F (22.7°C)Light RainMostly SunnySlightly HighSlightly High
May77.2°F (25.1°C)Light RainMostly SunnyAverageAverage
June80.6°F (27.0°C)Moderate RainMostly SunnyAverageAverage
July81.7°F (27.6°C)Moderate RainMostly SunnyAverageSlightly High
August81.9°F (27.7°C)Moderate RainMostly SunnySlightly LowAverage
September79.5°F (26.4°C)Moderate RainMostly SunnySlightly HighSlightly Low
October74.7°F (23.7°C)Light RainMostly SunnySlightly LowAverage
November68.0°F (20.0°C)No Rain (Dry)Mostly SunnySlightly LowAverage
December64.2°F (17.9°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient platform for you to plan new journeys, refine your existing arrangements, or manage your bookings with ease. Your saved or reserved properties are now neatly categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Delight in the lakeside landscape of Winter Haven

Enjoy the entertainment and other features of Winter Haven. This city's lake, gardens and baseball games draw many visitors. LEGOLAND® Florida and Reunion Resort Golf Course are just a couple of the must-see attractions in the area. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Winter Haven

Are you looking for attractions to visit during your stay? Venture out of your holiday home and experience everything that makes Winter Haven a fun place to get away to. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • LEGOLAND® Florida (3.2 mi / 5.2 km)
  • Reunion Resort Golf Course (19.3 mi / 31 km)
  • Peppa Pig Theme Park Florida (3.6 mi / 5.8 km)
  • Chain Of Wakes (4.1 mi / 6.6 km)
  • Lake Myrtle Sports Complex (7.4 mi / 12 km)
  • Southern Dunes Golf and Country Club (9.9 mi / 15.9 km)

Exploring the natural landscape of Winter Haven

Travellers enjoy Winter Haven for its lakeside setting and gardens. Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Winter Haven is a great place to get outside. These are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Auburndale City Park (4.5 mi / 7.3 km)
  • The Circle B Bar Reserve (8.8 mi / 14.2 km)
  • Star Lake (10.1 mi / 16.3 km)
  • Mary Holland Park (10.5 mi / 16.8 km)
  • Bok Tower Gardens (11.2 mi / 18 km)
  • Lake Parker (12.5 mi / 20.1 km)

Transport to and around Winter Haven

Fly into Lakeland Intl. Airport (LAL), the closest airport, located 17.3 mi (27.8 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Kissimmee, FL (ISM-Kissimmee Gateway), which is 26 mi (41.9 km) away.

If you'd prefer to travel by train, you can make your way to Winter Haven Station.

Frequently asked questions

What is the best area to stay in Winter Haven when booking a holiday rental?
When considering a holiday rental in Winter Haven, Florida, a popular area to stay is the downtown vicinity. This charming neighbourhood offers a delightful mix of local shops, restaurants, and a vibrant setting. One of the top attractions here is the beautiful Chain of Lakes, where visitors can enjoy scenic views, boating, and picnicking along the waterfront. Additionally, the nearby LEGOLAND Florida Resort provides a fun-filled experience for families and those young at heart, featuring rides, shows, and interactive attractions.

Another great option is the picturesque Cypress Gardens area, known for its stunning botanical gardens and serene landscapes. This area, steeped in history, is superb for those looking to unwind amidst nature while still being close to various amenities.
How much does it cost to rent a holiday home in Winter Haven?
Prices for holiday rentals in Winter Haven vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winter Haven to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winter Haven holiday house rentals?
You can find great discounts on house rentals in Winter Haven on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Winter Haven?
In Winter Haven, holiday houses are the most popular type of holiday rental, with around 440 available throughout the area. These properties typically offer spacious living arrangements, multiple bedrooms, and fully equipped kitchens, making them ideal for families or larger groups. Many also feature outdoor spaces such as private gardens or patios, great for enjoying the warm Florida weather. Additionally, there are about 100 apartments, which provide a more compact option for couples or solo travellers, often including amenities like pools and fitness centres. Cottages and villas, with 64 and 16 options respectively, offer a more quaint and relaxed atmosphere, while several condos can also be found, providing yet another alternative for visitors.
Are there any family house rentals in Winter Haven?
In Winter Haven, Florida, there is a substantial selection of family-friendly houses available, with around 101 options to choose from. This charming city is renowned for its beautiful chain of lakes, making it an appealing destination for families looking to enjoy water-based activities. Many of the homes feature spacious living areas, full kitchens, and outdoor patios or gardens, great for barbecues or simply unwinding after a day of adventure.

Families will find amenities such as Wi-Fi, air conditioning, and laundry facilities common in these properties, ensuring a comfortable and convenient stay. Additionally, the locale is near popular attractions like LEGOLAND Florida, which offers fun for all ages, and the serene Bok Tower Gardens, where visitors can explore lush landscapes and enjoy the famous carillon music.
Can I rent a holiday home with a pool or hot tub in Winter Haven?
In Winter Haven, there are many holiday homes available for rent that come with pools and hot tubs, with approximately 61 options to choose from. This picturesque city, known for its chain of lakes and pleasant weather, features various neighbourhoods where these rentals can be found, including the tranquil areas near Lake Eloise and the more vibrant spots close to Lake Howard.

Travellers can expect a range of amenities in these properties, such as private swimming pools, relaxing hot tubs, spacious outdoor patios, and fully equipped kitchens, ideal for enjoying both relaxation and social gatherings.
Can I find long-stay holiday rentals in Winter Haven?
A long-stay holiday rental in Winter Haven is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Winter Haven?
In Winter Haven, there is a wide selection of pet-friendly house rentals available, with around 54 options to choose from. These holiday homes often come equipped with amenities such as spacious backyards, modern kitchens, and comfortable living areas, making them ideal for families or groups travelling with pets. Many properties feature additional conveniences like laundry facilities, outdoor seating areas, and even private pools, enhancing the overall experience for pet owners.

The area is known for its beautiful lakes and parks, providing ample opportunities for outdoor activities with pets. Nearby, you can explore the scenic Chain of Lakes, which offers walking trails and picnic spots, superb for enjoying the Florida sunshine with your four-legged friends. Additionally, local pet-friendly cafes and shops contribute to a friendly setting for those travelling with pets.
Are there any remote work holiday rentals in Winter Haven?
In Winter Haven, there are numerous options for remote work holiday rentals, with around 572 available throughout the area. Many of these properties cater specifically to those needing a productive work environment, featuring amenities such as high-speed Wi-Fi, dedicated work desks, and comfortable chairs to ensure an efficient workspace.

The city is known for its picturesque Chain of Lakes, offering opportunities for outdoor activities during breaks from work. Additionally, many rentals include fully equipped kitchens, allowing guests to prepare meals conveniently. For those seeking a balanced work-life experience, the nearby attractions, such as Legoland Florida Resort and beautiful parks, provide ample opportunities for relaxation after a day of remote working. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winter Haven holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Winter Haven with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Winter Haven?
In Winter Haven, popular holiday rental amenities include well-equipped kitchens, ensuring guests can prepare their own meals. Onsite parking is typically available, making it convenient for those travelling with cars. Many rentals also feature coffee and tea makers, allowing visitors to enjoy a warm drink at their leisure. Additionally, outdoor spaces like decks or patios are common, providing a pleasant area to relax and unwind after a day of exploring the local attractions.
When is the best time to visit Winter Haven for a holiday rental?
The ideal time to visit Winter Haven for a holiday rental is during the peak season from February to April, with March standing out as the most popular month. This vibrant period attracts visitors looking for warmer weather and an abundance of outdoor activities. With temperatures typically ranging from 15 to 28 degrees Celsius, it's superb for enjoying the area's famous attractions, including the stunning Legoland Florida Resort and the beautiful Chain of Lakes.

During these months, you can expect a buzzing atmosphere filled with travellers, all eager to partake in the numerous recreational opportunities. From boating and fishing to exploring the local parks, there's something for everyone to enjoy in the mild sunshine.

If you're looking for a more budget-friendly option, November is a wonderful time to visit Winter Haven. This month offers a quieter experience, allowing you to explore the area's charming attractions without the crowds. The weather remains pleasant, making it a great time for leisurely strolls and enjoying the scenic views.

Ultimately, the best time to book your holiday rental in Winter Haven depends on your preferences for social atmosphere and outdoor activities.
How early should I book a Winter Haven holiday rental?
Book your Winter Haven holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Winter Haven?
In Winter Haven, visitors can enjoy a variety of attractions that highlight the area's unique charm. The most top is Legoland Florida Resort, a family-friendly set-up park that offers rides, shows, and interactive experiences based on the popular LEGO toy brand. This park is a major draw for families staying in the area and is located near several rental options.

For those interested in nature, the Chain of Lakes provides opportunities for boating, fishing, and scenic walks along the water. The surrounding parks, such as Lake Howard Nature Park, feature walking trails and picnic areas, superb for outdoor enthusiasts.

Additionally, downtown Winter Haven boasts a selection of shops, cafes, and restaurants, allowing visitors to experience local cuisine and culture. The historic area is also home to the beautiful theatre, which often hosts community events and performances.
Can I change or cancel my Winter Haven home rental booking on Vrbo?
To find Winter Haven holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Winter Haven holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More holiday ideas